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acetaldoxime
acetaldehyde oxime

Supplier Sponsors

Name:(NE)-N-ethylidenehydroxylamine
CAS Number: 107-29-9Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:203-479-6
FDA UNII: ME6U10SD7D
Nikkaji Web:J1.779.302K
Beilstein Number:1209252
MDL:MFCD00002124
XlogP3:-0.10 (est)
Molecular Weight:59.06805000
Formula:C2 H5 N O
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:information only not used for fragrances or flavors
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Soluble in:
 water, 1.772e+005 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Sigma-Aldrich
For experimental / research use only.
Acetaldehyde oxime, mixture of syn and anti 99%
TCI AMERICA
For experimental / research use only.
Acetaldoxime >99.0%(GC)
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intraperitoneal-mouse LD50 100 mg/kg
National Technical Information Service. Vol. AD277-689

unreported-mouse LD50 1150 mg/kg
Pharmaceutical Chemistry Journal Vol. 12, Pg. 227, 1978.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
information only not used for fragrances or flavors
Recommendation for acetaldoxime usage levels up to:
 not for fragrance use.
 
Recommendation for acetaldoxime flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):107-29-9
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5324279
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
(NE)-N-ethylidenehydroxylamine
Chemidplus:0000107299
EPA/NOAA CAMEO:hazardous materials
RTECS:AB2975000 for cas# 107-29-9
 
References:
 (NE)-N-ethylidenehydroxylamine
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5324279
Pubchem (cas):107-29-9
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
Metabolomics Database:Search
KEGG (GenomeNet):C02658
HMDB (The Human Metabolome Database):HMDB03656
FooDB:FDB023210
Export Tariff Code:2928.00.5000
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
 acetaldehyde oxime
 ethylidenehydroxylamine
(NE)-N-ethylidenehydroxylamine
 

Articles:

PubMed:Rhodococcus as A Versatile Biocatalyst in Organic Synthesis
PubMed:Aldoxime Metabolism Is Linked to Phenylpropanoid Production in Camelina sativa
PubMed:Gas chromatography-Fourier transform infrared spectroscopy reveals dynamic molecular interconversion of oximes
PubMed:Nitrile hydrolases
PubMed:Synthesis and crystal structure of (2S,4aR,8aR)-6-oxo-2,4a,6,8a-tetra-hydro-pyrano[3,2-b]pyran-2-carboxamide
PubMed:The Formation of a Camalexin Biosynthetic Metabolon
PubMed:Tyrosine biosynthesis, metabolism, and catabolism in plants
PubMed:Metabolism of indole-3-acetaldoxime in plants
PubMed:The unusual effect of pKM101 on the mutagenicity of acetaldehyde oxime in Salmonella typhimurium
PubMed:The maize cytochrome P450 CYP79A61 produces phenylacetaldoxime and indole-3-acetaldoxime in heterologous systems and might contribute to plant defense and auxin formation
PubMed:Cytochrome P450s as genes for crop improvement
PubMed:Controlled indole-3-acetaldoxime production through ethanol-induced expression of CYP79B2
PubMed:Vasorelaxant activity of some oxime derivatives
PubMed:Current aspects of auxin biosynthesis in plants
PubMed:Biosynthetic pathway of the phytohormone auxin in insects and screening of its inhibitors
PubMed:Evolution of camalexin and structurally related indolic compounds
PubMed:Cytochrome P450 CYP79B2 from Arabidopsis catalyzes the conversion of tryptophan to indole-3-acetaldoxime, a precursor of indole glucosinolates and indole-3-acetic acid
PubMed:Comparative reprotoxicity of three oximes
PubMed:Auxin biosynthesis in pea: characterization of the tryptamine pathway
PubMed:Short-term salt stress in Brassica rapa seedlings causes alterations in auxin metabolism
PubMed:Negative Regulation of Age-Related Developmental Leaf Senescence by the IAOx Pathway, PEN1, and PEN3
PubMed:Possible Interactions between the Biosynthetic Pathways of Indole Glucosinolate and Auxin
PubMed:IAOx induces the SUR phenotype and differential signalling from IAA under different types of nitrogen nutrition in Medicago truncatula roots
PubMed:The pathway of auxin biosynthesis in plants
PubMed:Evaluation of high-affinity phenyltetrahydroisoquinoline aldoximes, linked through anti-triazoles, as reactivators of phosphylated cholinesterases
PubMed:CYP79B1 from Sinapis alba converts tryptophan to indole-3-acetaldoxime
PubMed:Biochemical analyses of indole-3-acetaldoxime-dependent auxin biosynthesis in Arabidopsis
PubMed:New efficient imidazolium aldoxime reactivators for nerve agent-inhibited acetylcholinesterase
PubMed:Indolyl-3-acetaldoxime dehydratase from the phytopathogenic fungus Sclerotinia sclerotiorum: purification, characterization, and substrate specificity
PubMed:GH3 Auxin-Amido Synthetases Alter the Ratio of Indole-3-Acetic Acid and Phenylacetic Acid in Arabidopsis
PubMed:The Formation of a Camalexin Biosynthetic Metabolon
PubMed:Novel tryptophan metabolic pathways in auxin biosynthesis in silkworm
PubMed:Identification of an aldehyde oxidase involved in indole-3-acetic acid synthesis in Bombyx mori silk gland
PubMed:Relaxant effect of oxime derivatives in isolated rat aorta: role of nitric oxide (NO) formation in smooth muscle
PubMed:Functional interpretation and structural insights of Arabidopsis lyrata cytochrome P450 CYP71A13 involved in auxin synthesis
PubMed:A Novel Arabidopsis microRNA promotes IAA biosynthesis via the indole-3-acetaldoxime pathway by suppressing superroot1
PubMed:Development of a relative quantification method for infrared matrix-assisted laser desorption electrospray ionization mass spectrometry imaging of Arabidopsis seedlings
PubMed:Indole-3-acetaldoxime-derived compounds restrict root colonization in the beneficial interaction between Arabidopsis roots and the endophyte Piriformospora indica
PubMed:Oxidative effects in human erythrocytes caused by some oximes and hydroxylamine
PubMed:A "reactive" turn-on fluorescence probe for hypochlorous acid and its bioimaging application
PubMed:Arabidopsis mutants in the C-S lyase of glucosinolate biosynthesis establish a critical role for indole-3-acetaldoxime in auxin homeostasis
PubMed:Many roads lead to "auxin": of nitrilases, synthases, and amidases
PubMed:Arabidopsis cytochrome P450 monooxygenase 71A13 catalyzes the conversion of indole-3-acetaldoxime in camalexin synthesis
PubMed:Acetaldehyde Oxime, A Product Formed during the In Vivo Nitrate Reductase Assay of Soybean Leaves
PubMed:Alternative Route Toward Nitrones: Experimental and Theoretical Findings
PubMed:The involvement of two p450 enzymes, CYP83B1 and CYP83A1, in auxin homeostasis and glucosinolate biosynthesis
PubMed:Overview of screening for new microbial catalysts and their uses in organic synthesis--selection and optimization of biocatalysts
PubMed:Synthesis and fungistatic activity of aryl aldoxime derivatives
PubMed:Potent 3-Hydroxy-2-Pyridine Aldoxime Reactivators of Organophosphate-Inhibited Cholinesterases with Predicted Blood-Brain Barrier Penetration
PubMed:Vapor-phase Beckmann rearrangement of oxime molecules over H-Faujasite zeolite
PubMed:Probing crucial metabolic pathways in fungal pathogens of crucifers: biotransformation of indole-3-acetaldoxime, 4-hydroxyphenylacetaldoxime, and their metabolites
PubMed:Overproduction and characterization of the first enzyme of a new aldoxime dehydratase family in Bradyrhizobium sp
PubMed:CYP83B1, a cytochrome P450 at the metabolic branch point in auxin and indole glucosinolate biosynthesis in Arabidopsis
PubMed:Camalexin is synthesized from indole-3-acetaldoxime, a key branching point between primary and secondary metabolism in Arabidopsis
PubMed:Indole Glucosinolate Biosynthesis Limits Phenylpropanoid Accumulation in Arabidopsis thaliana
PubMed:New insight into the biosynthesis and regulation of indole compounds in Arabidopsis thaliana
PubMed:7-Dialkylaminocoumarin Oximates: Small Molecule Fluorescent "Turn-On" Chemosensors for Low-Level Water Content in Aprotic Organic Solvents
PubMed:Biotransformation of isonitrosoacetophenone (2-keto-2-phenyl-acetaldoxime) in tobacco cell suspensions
PubMed:Chemicals mutagenic in Salmonella typhimurium strain TA1535 but not in TA100
PubMed:Synthesis, structure, DFT calculations, electrochemistry, fluorescence, DNA binding and molecular docking aspects of a novel oxime based ligand and its palladium(II) complex
PubMed:Cellular localization of the Arabidopsis class 2 phytoglobin influences somatic embryogenesis
PubMed:CYP79 P450 monooxygenases in gymnosperms: CYP79A118 is associated with the formation of taxiphyllin in Taxus baccata
PubMed:Substantial reprogramming of the Eutrema salsugineum (Thellungiella salsuginea) transcriptome in response to UV and silver nitrate challenge
PubMed:Arabidopsis gulliver1/SUPERROOT2-7 identifies a metabolic basis for auxin and brassinosteroid synergy
PubMed:The Biosynthetic Pathway of Indole-3-Carbaldehyde and Indole-3-Carboxylic Acid Derivatives in Arabidopsis
PubMed:Redirection of tryptophan metabolism in tobacco by ectopic expression of an Arabidopsis indolic glucosinolate biosynthetic gene
PubMed:Nitric Oxide and Nitrous Oxide Production by Soybean and Winged Bean during the in Vivo Nitrate Reductase Assay
PubMed:Quaternary and tertiary aldoxime antidotes for organophosphate exposure in a zebrafish model system
PubMed:The role of MYB34, MYB51 and MYB122 in the regulation of camalexin biosynthesis in Arabidopsis thaliana
PubMed:Metabolomic analysis of isonitrosoacetophenone-induced perturbations in phenolic metabolism of Nicotiana tabacum cells
PubMed:Green synthesis of CuO nanoparticles by aqueous extract of Gundelia tournefortii and evaluation of their catalytic activity for the synthesis of N-monosubstituted ureas and reduction of 4-nitrophenol
PubMed:Roles of YUCCAs in auxin biosynthesis and drought stress responses in plants
PubMed:Detection of some volatile degradation products released during photoexposition of ranitidine in a solid state
PubMed:A fungal-responsive MAPK cascade regulates phytoalexin biosynthesis in Arabidopsis
PubMed:The Thiol Reductase Activity of YUCCA6 Mediates Delayed Leaf Senescence by Regulating Genes Involved in Auxin Redistribution
PubMed:Cytochrome P450 CYP71AT96 catalyses the final step of herbivore-induced phenylacetonitrile biosynthesis in the giant knotweed, Fallopia sachalinensis
PubMed:Structures of reduced and ligand-bound nitric oxide reductase provide insights into functional differences in respiratory enzymes
PubMed:Novel tryptophan metabolism by a potential gene cluster that is widely distributed among actinomycetes
PubMed:Arabidopsis NITRILASE 1 Contributes to the Regulation of Root Growth and Development through Modulation of Auxin Biosynthesis in Seedlings
PubMed:CYP79D enzymes contribute to jasmonic acid-induced formation of aldoximes and other nitrogenous volatiles in two Erythroxylum species
PubMed:Regulation of Pathogen-Triggered Tryptophan Metabolism in Arabidopsis thaliana by MYB Transcription Factors and Indole Glucosinolate Conversion Products
PubMed:Nitrilase in biosynthesis of the plant hormone indole-3-acetic acid from indole-3-acetonitrile: cloning of the Alcaligenes gene and site-directed mutagenesis of cysteine residues
PubMed:TRANSCRIPTION ACTIVATOR-LIKE EFFECTOR NUCLEASE-Mediated Generation and Metabolic Analysis of Camalexin-Deficient cyp71a12 cyp71a13 Double Knockout Lines
PubMed:CYP71B15 (PAD3) catalyzes the final step in camalexin biosynthesis
PubMed:Why is the oxidation state of iron crucial for the activity of heme-dependent aldoxime dehydratase? A QM/MM study
PubMed:The biosynthetic pathway of crucifer phytoalexins and phytoanticipins: de novo incorporation of deuterated tryptophans and quasi-natural compounds
PubMed:Design, synthesis and biological evaluation of novel tetrahydroacridine pyridine- aldoxime and -amidoxime hybrids as efficient uncharged reactivators of nerve agent-inhibited human acetylcholinesterase
PubMed:Characterization of a nitrilase and a nitrile hydratase from Pseudomonas sp. strain UW4 that converts indole-3-acetonitrile to indole-3-acetic acid
PubMed:Chronic carcinogenesis studies of acrolein and related compounds
PubMed:Lipoamide dehydrogenase and diaphorase catalyzed conversion of some NO donors to NO and reduction of NO scavenger 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide (PTIO)
PubMed:Dehydration of Aldoximes Using PhSe(O)OH as the Pre-Catalyst in Air
PubMed:Herbivore-induced poplar cytochrome P450 enzymes of the CYP71 family convert aldoximes to nitriles which repel a generalist caterpillar
PubMed:Cyanogenesis in glucosinolate-producing plants: Carica papaya and Carica quercifolia
PubMed:The role of cytochrome P450 enzymes in the biosynthesis of camalexin
PubMed:Decontamination of chemical and biological warfare agents with a single multi-functional material
PubMed:Arabidopsis cytochrome P450s that catalyze the first step of tryptophan-dependent indole-3-acetic acid biosynthesis
PubMed:Hydroxamic acids as a novel family of serine racemase inhibitors: mechanistic analysis reveals different modes of interaction with the pyridoxal-5'-phosphate cofactor
PubMed:Nitrite formation from hydroxylamine and oximes by Pseudomonas aeruginosa
PubMed:Metabolic studies on N-methylpyridinium-2-aldoxime. I. The conversion to thiocyanate
PubMed:The biosynthesis of cyanogenic glucosides in higher plants. Identification of three hydroxylation steps in the biosynthesis of dhurrin in Sorghum bicolor (L.) Moench and the involvement of 1-ACI-nitro-2-(p-hydroxyp
PubMed:Chemical defenses of crucifers: elicitation and metabolism of phytoalexins and indole-3-acetonitrile in brown mustard and turnip
PubMed:Inhibition of copper amine oxidases by pyridine-derived aldoximes and ketoximes
PubMed:Identification of crucial histidines involved in carbon-nitrogen triple bond synthesis by aldoxime dehydratase
PubMed:Trp-dependent auxin biosynthesis in Arabidopsis: involvement of cytochrome P450s CYP79B2 and CYP79B3
PubMed:Multivariate statistical models of metabolomic data reveals different metabolite distribution patterns in isonitrosoacetophenone-elicited Nicotiana tabacum and Sorghum bicolor cells
PubMed:O-Substituted derivatives of pralidoxime: muscarinic properties and protection against soman effects in rats
PubMed:CYP83A1 and CYP83B1, two nonredundant cytochrome P450 enzymes metabolizing oximes in the biosynthesis of glucosinolates in Arabidopsis
PubMed:Genotoxicity of 6 oxime compounds in the salmonella/mammalian-microsome assay and mouse lymphoma TK +/- assay
PubMed:DOF transcription factor AtDof1.1 (OBP2) is part of a regulatory network controlling glucosinolate biosynthesis in Arabidopsis
PubMed:Assembling the biosynthetic puzzle of crucifer metabolites: indole-3-acetaldoxime is incorporated efficiently into phytoalexins but glucobrassicin is not
PubMed:Nitric Oxide Emissions from Soybean Leaves during in Vivo Nitrate Reductase Assays
PubMed:Regulation of aldoxime dehydratase activity by redox-dependent change in the coordination structure of the aldoxime-heme complex
PubMed:A gene cluster responsible for alkylaldoxime metabolism coexisting with nitrile hydratase and amidase in Rhodococcus globerulus A-4
PubMed:Ab initio molecular electrostatic potentials of perillartine analogues: implications for sweet-taste receptor recognition
PubMed:Nitrile hydratase involved in aldoxime metabolism from Rhodococcus sp. strain YH3-3 purification and characterization
PubMed:Distribution of aldoxime dehydratase in microorganisms
PubMed:Purification and characterization of recombinant cytochrome P450TYR expressed at high levels in Escherichia coli
PubMed:[Oxidases and oxygenases in higher plants, I. On the occurrence of indolyl-(3)-acetaldehyde oxime and its formation from L-tryptophan]
PubMed:Synthesis, Spectroscopic, Structural and Quantum Chemical Studies of a New Imine Oxime and Its Palladium(II) Complex: Hydrolysis Mechanism
PubMed:The presence of CYP79 homologues in glucosinolate-producing plants shows evolutionary conservation of the enzymes in the conversion of amino acid to aldoxime in the biosynthesis of cyanogenic glucosides and glucosi
PubMed:Investigation of methyl pyridinium-2-aldoxime salts
PubMed:Biosynthetic origin of BE-10988 in Streptomyces sp. BA10988
PubMed:Detoxification of tabun at physiological pH mediated by substituted ?-cyclodextrin and glucose derivatives containing oxime groups
PubMed:Biosynthesis of indole-3-acetic acid in tomato shoots: Measurement, mass-spectral identification and incorporation of (-2)H from (-2)H 2O into indole-3-acetic acid, D- and L-tryptophan, indole-3-pyruvate and trypta
PubMed:Prophage induction in lysogenic Escherichia coli with simple hydroxylamine and hydrazine compounds
PubMed:Anhydrous hydration of nitriles to amides using aldoximes as the water source
PubMed:Studies on the mechanisms of induction of N-nitrosodimethylamine demethylase by fasting, acetone, and ethanol
PubMed:Anion-driven conformation control and enhanced sulfate binding utilising aryl linked salicylaldoxime dicopper helicates
PubMed:Synthesis, biological evaluation, and molecular docking studies of 2,6-dinitro-4-(trifluoromethyl)phenoxysalicylaldoxime derivatives as novel antitubulin agents
PubMed:Time-resolved cryogenic modulation reveals isomer interconversion profiles in dynamic chromatography
PubMed:Postsynthesis-Treated Iron-Based Metal-Organic Frameworks as Selective Catalysts for the Sustainable Synthesis of Nitriles
PubMed:Unveiling the phytoalexin biosynthetic puzzle in salt cress: unprecedented incorporation of glucobrassicin into wasalexins A and B
PubMed:The effect of an aldoxime on acute sarin poisoning
PubMed:Parathion (bladan) poisoning treated with 2-PAM (pyridyl-2-aldoxime methyl iodide): case report
PubMed:Polymerase chain reaction for identification of aldoxime dehydratase in aldoxime- or nitrile-degrading microorganisms
PubMed:Phytoalexins from the crucifer rutabaga: structures, syntheses, biosyntheses, and antifungal activity
PubMed:Tungstate sulfuric acid (TSA)/KMnO4 as a novel heterogeneous system for rapid deoximation
PubMed:Extremely long protection by pyrazole derivatives against chemically induced gastric mucosal injury
PubMed:Nonquaternary cholinesterase reactivators. 3. 3(5)-Substituted 1,2,4-oxadiazol-5(3)-aldoximes and 1,2,4-oxadiazole-5(3)-thiocarbohydroximates as reactivators of organophosphonate-inhibited eel and human acetylcholi
PubMed:Minimum concentrations of N-methylpyridinium-2-aldoxime methane sulphonate (P2S) which reverse neuromuscular block
PubMed:The chronic toxicity of N-methylpyridinium-2-aldoxime methane sulphonate (P2S), a reactivator of phosphorylate cholinesterase
PubMed:[Parathion poisoning treated with picoline-2-aldoxime iodide]
PubMed:Solid phase asymmetric synthesis of isoxazolines
PubMed:Simulation of elution profiles for two-dimensional dynamic gas chromatographic experiments
PubMed:Aldoximes: active-site probes of alcohol dehydrogenases
PubMed:Systematic regulation of the enzymatic activity of phenylacetaldoxime dehydratase by exogenous ligands
PubMed:Studies of nitrile oxide cycloadditions, and the phenolic oxidative coupling of vanillin aldoxime by Geobacillus sp. DDS012 from Italian rye grass silage
PubMed:[Investigations for obtaining compounds with potential antiinflammatory action, carboxymethylic ethers of some oximes]
PubMed:Studies on the renal elimination of N-methylpyridinium-2-aldoxime
PubMed:[The synthesis of aldoxime ester derivatives with biological activity]
PubMed:In vitro reactivation and "ageing" of Tabuninhibited blood cholinesterases; studies with N-methyl-pyridinium-2-aldoxime methane sulphonate and N,N'-trimethylene bis (pyridinium-4-aldoxime) dibromide
PubMed:[Action of N-dodecylpyridine-2-aldoxime (2 PAD) and of N-methylpyridine-2-aldoxime (2 PAM) on the characteristics of permeability of isolated frog skin]
PubMed:[ALPHA-PYRIDYL-ALDOXIME SULFOMETHYLATE (7676 RP) PER OS, IN THE PREVENTION OF ACUTE ORAL POISONING WITH MALATHON]
PubMed:Sweet-taste receptor recognition of the conformationally flexible aldoxime molecule
PubMed:Metabolic studies on N-methylpridinium-2-aldoxime. II. The conversion to N-methylpyridinium-2-nitrile
PubMed:Metabolic studies on N-methylpyridinium-2-aldoxime. III. Experiments with the 14C-labelled compound
PubMed:[Reactivation of cholinesterase with pyridinium aldoximes during their combined covalent immobilization in polymeric hydrogels]
PubMed:The action of an aldoxime (2-pyridine aldoxime methiodide) on acute alkylphosphate poisoning in mice
PubMed:Effect of pyridine aldoximes on response of frog rectus muscle to acetylcholine
PubMed:The effect of pyridine aldoxime dodecyliodide on monamine oxidase and bound amines
 
Notes:
An oxime is one in a class of chemical compounds with the general formula R1R2CNOH, where R1 is an organic side chain and R2 is either hydrogen, forming an aldoxime, or another organic group, forming a ketoxime. [HMDB]
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